


The Devil's Tail

by KinknFetish



Category: Supernatural
Genre: Alternate Universe, Anal Sex, Cock Cages, Destiel - Freeform, M/M, Multi, Nipple Clamps, Oral Sex, Pole Dancing, Riding Crop, Sastiel - Freeform, Sounding, Spanking, St. Andrew's Cross, Tail Kink, Threesome - M/M/M, Voyeurism, Wax Play, Whipping, Wincest - Freeform, Wing Kink, corset kink, flogger, spreader bar
Language: English
Status: Completed
Published: 2015-01-02
Updated: 2015-01-08
Packaged: 2018-03-05 00:37:22
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 18,447
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3098468
Author URL: https://archiveofourown.org/users/KinknFetish/pseuds/KinknFetish
Summary: <blockquote class="userstuff">
              <p>AU Lucifer and Death grow weary of the Winchester Brothers interfering with the breaking of the seals to bring on the end of the world. Lucifer bestows a Devil's Tail on Dean as a distraction from the Apocalypse to keep him and Sam out of the dark duos way. The Tail is sentient and has a huge appetite for sins of the flesh. Will Sam and Castiel fall under the intoxicating sensual spell of the Devil's Tail and give up the fight to stop the breaking of the seals?</p>
            </blockquote>





	1. Transformation

 

 **The Devil's Tail** **Part One**

A knock at the motel room door woke Dean from a sound and dreamless sleep. He was warm and content snuggled up to Sam's broad back and he didn't want to get up. The knock sounded again louder and more insistent. Dean growled deep in his throat and got out of bed. Sam shifted a little but didn't wake up. Dean grabbed a pair of boxer briefs off the floor not caring if they were his or Sam's and tugged them on. He glanced at the read out on the digital clock 3:33 in the morning. Dean was fairly sure that a visitor at that time of the morning could only mean bad news. He hid his gun behind his back as he opened the door.

Lucifer used his power to force Dean's body back from the doorway. He stepped inside the drab charmless room and smiled at Dean. “Death and I have decided that you and Sam are a festering thorn in our collective side. We agreed that you needed to be distracted while certain prophecies are fulfilled. Never let it be said that I don't have a certain perverse sense of humor.” Lucifer pressed his hand against Dean's stomach for a moment. When he pulled back, he was smiling like a shark. “I wish I could stay and watch the show but I've got places to go and prophecies to fulfill.” Suddenly the space Lucifer had inhabited was vacant and the motel room door was shut firmly in his wake.

Dean felt a warm liquid tingling sensation at the base of his spine. Then he felt a rather odd sensation as if the skin there was moving without his command or consent. He tried to look around but in the dimness of the room he couldn't see anything. Dean strode into the bathroom, shut the door and turned on the lights. He looked in the mirror and could see something growing out of the base of his spine. It was pulsing and lengthening. Dean watched in silent horror as it grew and grew. His mind was rejecting the reality of this. He must be dreaming. This was a nightmare brought on by a bucket of chicken wings, a bottle of tequila, and watching a Monstervision Marathon on TNT.

Dean closed his eyes counted to five and opened them again. The tail was over three feet long and the tip of it had become triangular like a 3D arrowhead. Dean stared at in the mirror for a moment, then the thick appendage moved. The tail slithered across Dean's hip then angled down to slide suggestively across his dick which went instantly hard. The trianglar tip of the tail teased the sensitive spot under the head of his penis until beads of pre come formed. Then, the tail caressed his balls and teased it's way between his cheeks to nudge his entrance. Dean grabbed hold of the tail and pulled it away from his body. He was shocked at the velvety muscular feel of it. It was like a giant flexible cock. Dean stared at the tail as it moved in his hands the arrowhead tip seeking and stimulating his right nipple til it was erect and sensitive.

Dean was fascinated and repulsed at the same time. What the hell had Lucifer done to him? How was he going to hide this fucking thing from Sammy? At the thought of Sam, the tail went rigid in Dean's grasp. Dean felt his cock twitch and a sudden fierce desire for Sam overwhelmed him. He flicked off the light and walked out into the dingy motel room. Sam was lying on his stomach now still sleeping deeply. Dean walked closer to the bed and leaned towards him. The tail flipped back the covers exposing Sam's nude body to Dean's hungry gaze. Dean emitted a low growl of pure sexual need for possession of his brother.

Dean pushed off the boxers and climbed onto the bed. The tail was caressing Sam's muscular back and ass. Dean's eyes were blown black and his face was set in a mask of lust. He grabbed the lube off the bed side table and slicked up the tail. Somehow the tail had transmitted it's desires directly into Dean's mind and Dean was totally on board with the plan. Dean put the lube aside and started to kiss Sam. Sam woke up and rolled on his side to face Dean.

“What time is it?” Sam looked a little sleep dazed in the dim light.

“Time for an oral favor.” Dean purred in a voice a couple octaves deeper than usual.

The tone and timbre of that voice sent shivers of desire down Sam's spine and he was instantly hard. It was amazing. After all these years, Dean could still do that to him without even touching him. Dean kissed him deeply and let his hands roam over smooth tanned skin. Sam returned the kiss with ferver and traced his fingers down honey toned freckled skin. When breathing became necessary, they pulled apart and Sam started to kiss, lick and nip his way down Dean's neck to his chest. When Sam reached Dean's already erect nipples, he looked up at Dean with a quirked brow. Dean just smirked and gently pushed Sam's head down. His smile deepened as Sam reached his navel and dipped his tongue inside suggestively. Dean couldn't wait to see how Sammy was gonna respond to the tail. Sam reached Dean's rock hard cock and he swirled his tongue over the crown to gather all the pearls of come gathered there. His eyes held Dean's as he did this. When Sam took Dean deep in his mouth, the tail nudged at Sam's opening. Sam's eyes got huge and he pulled off Dean.

“Dean, what the hell is that?” Sam choked out as he looked back at the tail.

“Well, Sammy, Lucifer paid me a little visit earlier tonight. It appears he has a twisted sense of humor. He and Death decided that we needed to be distracted so he gave me a Devil's Tail. It's kind of a longer, harder, pointier penis and it really likes you, Sammy.” Dean flashed him a wicked grin. His eyes twinkling with mirth and desire.

The tail chose that moment to enter Sam and proceed directly to the bundle of nerves that had Sam gasping with reaction. “What the Christ, Dean? That uh, oh God.....” Sam's eyes were blown wide and he stopped being able to form a coherent sentence. The tail was pulsing, turning and thrusting inside him moving in ways that would be impossible for a human partner.

“Time to finish what you started, Sammy.” Dean angled Sam's mouth over his cock and thrust into him.

Sam was overwhelmed with the sensation of having the tail and Dean's dick inside him. It was deliciously twisted, incredibly erotic and one hell of a distraction. They just might spend the rest of the apocalypse right here in this motel room.

*-*-*-*-

After a two hour marathon sex session, the sun was rising and Dean and Sam were ravenous and needed to replenish their bodily fluids. The motel was outside a small town on the far side of no where. Dean had laughingly referred to it as Spankfield cause the only thing to do here was spank your monkey. The tail had playfully swatted Sam's behind and taken notice of the bolt of desire that flashed through Sam with the impact. They decided Dean couldn't go out for provisions cause they had no idea what the tail might do. Sam showered first and left while Dean was still in the bathroom.

When Dean came out of the shower wrapped in an incredibly small motel towel, Castiel was right in front of him. “Son of a Bitch! You know I freaking hate when you do that.”

Castiel looked at him sapphire blue eyes appraising his charge cooly. “You have a Devil's Tail, Dean.”

“No shit Sherlock. Tell me something I don't know.” Dean shot back at the angel.

“The tail could be permanent or transitory depending on Lucifer's intent.” Castiel was still standing only inches away from Dean. He had never figured out the whole personal space issue.

The tail had been making a thorough appraisal of the angel. It was frustrated by the many layers of clothing the angel wore. It hooked itself under the collar of the ever present trench coat and sent it falling to the motel room floor to be closely followed by the suit jacket and tie.

“Your Devil's Tail is disrobing me, Dean. It's distracting.” Castiel announced looking into Dean's jewel toned eyes somberly.

“What are you gonna do about it, Angelcakes?” Dean asked with a wicked grin.

The tail had sent it's thoughts to Dean and Dean couldn't wait to see how Cas was going to respond.

The tail was pressing against the crease of Castiel's ass through his suit pants. Cas looked down at the rather obvious bulge at his crotch. “That's curious. This vessel hasn't had that reaction to being touched before.” The angel's voice sounded awed by this unique sensation.

The tail slid into the waste band of Castiel's pants and down the curve of his tight ass til it could tease and tickle his opening. The angel sucked in air and stared at Dean with wide startled eyes. “Dean, what is it doing?”

That expression on Castiel's usual wooden visage made Dean laugh heartily. The tail continued to tease at the tight bud of Castiel's opening and the angel noticed that his vessel's penis was now painfully hard. “Dean?” There was a note of arousal along with the pleading for understanding in the angel's deep rich voice.

“It's okay, Angelcakes. You're really going to enjoy this.” Dean leaned in and took advantage of the angel's parted lips to deeply invade his mouth. He started moving the angel steadily backwards until they reached the bed. Dean pulled away and Castiel followed his lips trying to recapture the amazing sensation of Dean's mouth on his and Dean's tongue exploring him. Jade green eyes clashed with sapphire blue as the faced each other breathing heavily.

“Strip, Cas.” Dean's voice was deep and tinged with a hint of dark intent. Castiel immediately complied exposing his slim taut body to the hunter's hungry gaze. “Lay back on the bed.” Dean's eyes followed Cas as he positioned himself in the center of the bed. The sight of the naked and obviously aroused angel had turned Dean's eyes black with lust. He climbed up the bed grabbed the lube and slicked the tail. He put the tube back and straddled the pale angel.

“Hold your arms out.” Castiel did as he was told too overwhelmed by what was happening to question Dean's commands. Dean moved up until his knees were pinning Castiel's shoulder's to the bed. “I've wanted to do this for a very long time. Open wide, Angelcakes, I'm coming in.” Cas opened up and Dean pressed his rock hard cock deep inside the angel's mouth. Cas licked around the hard shaft and started to suck as Dean began to thrust in and out of the wet heat.

The tail had been teasing at Castiel's entrance until now and it thrust inside. Castiel's hips arched up and he felt a current of raw sexual energy jolt his vessel. He moaned around Dean's dick and started to suck harder. “Yeah, that's it Angelcakes. I knew you were more than just a holy tax accountant under that damn trench coat!” Dean's head was thrown back. He was practically purring with pleasure.

Sam pushed open the door and was momentarily stunned by the sight of his brother with Castiel. “Dean, what the hell are you doing?” Sam demanded, bitch face firmly in place.

“I'm enjoying a double slice of Angel food cake and he is delicious.” Dean answered looking over his shoulder at Sam with a lascivious grin.

This was all kinds of wrong but Sam couldn't help but feeling turned on by the sight of his brother and the Devil's Tail ravishing Castiel. He put the food and drinks on the small table in the corner of the room then turned back to the bed. His eyes darkened as he started to unbutton his shirt.

The tail was driving Castiel to the brink then backing off as it worked with Dean to make the angel crazy with desire. Dean's head was thrown back, his lips parted making soft sounds as he enjoyed the hot wet perfection of Castiel's mouth.

Sam finished undressing and crawled on the bed with Dean and Cas. He lowered his head and licked up the inside of Castiel's thigh making the angel's hips surge up in response. Sam smiled and turned his head to lick up the other side to the angel's hip bone. He bit down then licked the spot to ease the sting. He really liked the idea of marking the angel who had left a brand on his brother. Sam had always been jealous of that mark and he was going to make Cas pay a little for it now. He continued biting and licking across Castiel's stomach then to the other hip where he bit down hard. The angel's hips surged up again and Sam licked away the sting. Sam painted a broad stripe with his tongue up the underside of Castiel's weeping cock. This time he had the angel's hips pinned with his huge hands. He took Castiel deep in his throat and set up a counter rhythm to the Devil's Tail.

Castiel's vessel was overloaded with sensations and impulses. It was all too damn much and he felt like we was going to explode with the enormity of it all. He felt the rhythm of Dean's thrusts change and he started to suck harder.

“Fuck, Cas. I'm gonna come.” Dean started to pull free but Cas continued sucking and tilted his head to follow Dean's movement. Dean gave in and let his orgasm tear trough him and flood the angel's mouth.

At that moment, the tail was mercilessly stimulating the bundle of nerves that made Castiel come hard in Sam's mouth. The angel's body shuddered and trembled as he rode out the wave of his orgasm. Sam pulled away and Dean pulled back as the tail left Castiel. Sam got on one side of Cas while Dean lay on the other. Dean reached out and gently traced Castiel's swollen lips with is fingertip. “Angelcakes, that was freaking awesome.” Dean leaned in and gently kissed Cas. Delving in deeper, he captured the angel's tongue and sucked the taste of himself off it.

Sam raised a brow at the 'Angelcakes' but had to agree it had been pretty sweet. Dean looked up at him as he broke the kiss. He smiled at Sam and leaned across Cas to soul kiss him. Sam returned the kiss and licked deeply into his bothers mouth. Somehow this all felt right even though Sam knew somewhere deep inside that it was definitely wrong. Dean finally pulled away and Sam noticed how tired he looked. Dean curled up against Castiel's side. Sam threw one leg across the angel's and his arm across Castiel's waist as they settled in and took a much needed nap.

Castiel was sandwiched between the Winchester's listening to their even breathing as they slept. There were a lot of thoughts whirring through his head as their strong heart beats filled his ears. He was an angel. He could have stopped what happened. Why didn't he stop it? He looked appraisingly at Dean and Sam's sleeping faces. They looked younger and more vulnerable when they were at rest. Their lives had been shadowed by tragedy and many counted sorrows. Somehow, these wounded warriors had made Cas feel. Castiel knew the answer to why he hadn't stopped it, had known it for quite some time. He loved the Winchester brothers. He wanted to protect them, comfort them, and yes experience the pleasures of the flesh with them. Castiel felt a bit overwhelmed by the truth of the situation. He felt wetness on his cheeks and understood that his vessel was crying with the depth of his feelings. Castiel could no longer fight the rising tide of emotions within him. He had to leave them, order his thoughts and focus his energy. He had to find a way to banish the Devil's Tail or lose himself completely.  
  


 


	2. Spanks for the Memories

 

**The Devil's Tail Part Two  
**

**Spanks for the Memories**

 

Sam woke up first. He noticed that Cas was gone and felt a small pang of loss. He had wanted to play with Cas, Dean and the Devil's Tail again. His body made it's need for food and drink known and he slipped out of bed to heat up the food he had brought in a few hours ago. The smell of the food pulled Dean from his slumber. He woke up horny, hungry and thirsty in that order. The Devil's Tail seemed to understand that Dean needed to take care of the eating and drinking so he could be ready for another long session of hardcore fucking. Sam eyed Dean warily as he made his way to the table and sat down. Dean caught his eye and tipped him a wink and smirk. His jewel toned eyed glittered with mirth. It was strange how neither one of them seemed the least bit awkward about doing all this while completely nude.

Sam stood up and announced he was going to take a shower and made his way casually into the small motel bathroom. Dean watched him go appreciating the view. The Devil's Tail hardened and telegraphed some deliciously dirty thoughts into Dean's lust fevered brain. By the time Dean finished eating, Sam was emerging from the bathroom wrapped in a ridiculously small towel leaving a luscious amount of tanned glistening skin on display. All thoughts of a shower evaporated from Dean's mind as he stood up and crossed the distance between himself and Sam.

“Sammy...” Dean cupped Sam's face in his hands and kissed him deeply his lips soft and yielding as the Devi's Tail was hard and demanding. Their cocks were already rigid with arousal and grinding against each other. The friction was a delicious tease but not nearly enough for either of them or the Tail. Dean pulled back from the kiss slowly, capturing Sam's bottom lip in his teeth then biting down hard. The unexpected pain jolted through Sam and made him inexplicably harder. Dean released Sam's lip and pulled back to look into Sam's glowing blue, green, gold eyes. There was something dark and dangerous in Dean's intense stare. Sam was caught in that hard stare that seemed to look inside him and through him. He felt something building between them and his heart started to beat faster with anticipation. Dean suddenly broke the stare and walked over to his duffle bag. He rummaged in a side compartment drew out a few items and turned back towards Sam. Dean threw Sam a silver cock ring. He caught it easily and put it on without question. Sam froze in place looking at Dean with a mix of anticipation and desire. His cock hard and jutting out, the silver cock ring wrapped tightly around the throbbing flesh.  
  
“Come here, Baby.” Dean commanded in that deep tone that made Sam's dick twitch.  
  
Sam stepped toward him hesitantly, his eyes were nervous. He wanted whatever this was turning into, but Sam wasn’t used to being vulnerable…not like this. It lit a fire in Dean’s gut. As Sam stopped before him, Dean stroked a hand over his cheek as the tail traced patterns on his back and down to his muscular ass.  
  
“Before we go any further, Sam, I need to make something very clear. I need to know that you understand what is about to happen.”  
  
Sam swallowed and licked his lips nervously as his eyes caught Dean’s. He didn’t speak, only nodded. “This isn’t a game. I’m very serious about this.” Sam was panting, lips parted. Desire and lust rolled off of him in waves. “You give yourself to me completely.” Dean licked his lips and put a hand to Sam’s chin, tugging it to make sure Sam was with him. “In return, I will give you everything you need…always.”  
  
If not for the cock ring, Dean thinks Sam might have come right there from the way his body undulated and he groaned. “Christ, Sam.” Dean murmured and it’s Sam’s turn to smile, although it was tentative. “You can't fuck any more skanky demon bitches. Not if you want to continue fucking me and Angelcakes.” Dean looked into his brother’s eyes, wanting to know he understood. Sam’s jaw worked, tightened, loosened and he swallowed hard.  
  
“Answer me. Do you understand?” Dean demanded his voice a terse growl.  
  
Sam’s “Yes,” was breathy and filled with need and Dean nearly lost his own control, nearly creamed his shorts because this was his Sammy submitting. Sam giving himself to Dean and my dear sweet lord was that hot!  
  
Dean breathed through it, and when he was sure that a simple touch wouldn't push him over the edge, he closed the space between them and kissed Sam. It was soft, like a promise. Sam’s lips yield to Deans tongue, and Dean moaned with the effort to pull away, to move them to what had to happen next. What the Devil's Tail had implanted in Dean's mind hours before. Dean stepped back and sat down on the edge of the bed.  
  
“Come here.” He commanded. What he and the Devil's Tail had planned would test everything between them.  
  
Sam stood in front of him, his cock almost at eye level oozing pre-come. “Now, I’m going to punish you Sam.” He couldn't believe the way Sam’s dick twitched when he said it. The Devil's Tail had definitely been right. Sam wanted this. “Over my knee.”  
  
For a minute neither of them moved then Sam was beside him, leaning over and Dean spread his legs open, arranging his brother so that Sam's cock hung down between them, his ass up turned over Dean’s right thigh.  
  
Dean’s own cock was straining now cause this was too fucking hot for words. One of Sam’s hands was fisted in the bedspread, the other was curled around Dean’s leg. Dean brought one hand up, over Sam’s naked thighs, caressing and soft up to his ass cheeks, gentle, tender. He felt Sam relax, then lifted his hand and brought it down lightly. The Devil's Tail had wrapped part of itself around Dean's aching cock then disappeared in the space between Dean's thighs to caress Sam's throbbing prick. Sam gasped and bit down on his lower lip. His body tightened up and Dean went back to the gentle massaging motion before smacking down a little harder on Sam's firm ass. Sam jerked this time and Dean could feel his brother’s cock wrapped in the velvety Devil's Tail bang against him.  
  
Sam was quiet, but the heat pouring off of him spoke volumes. Dean smacked him again, leaving a perfect red hand print on his brother’s right cheek. Sam groaned and his body quivered. “You're my fuck toy now, Sammy.” Dean purred “No more demon whores for you.” The next slap fell on his left ass cheek and Dean could feel the moan in Sam’s chest. “Say you're my fuck toy.”  
  
When Sam didn’t answer, Dean slapped him again, harder than before, on the tender skin just below his ass. “Answer me, Bitch!”  
  
“Y—Yes Dean.”  
  
“Yes what?”  
  
A sheen of sweat slicked Sam’s back as he tried to balance, tried to control the way he’s draped across Dean. He wanted to ease the humiliation of being bent over his brother’s knee, naked and hard and about to come…about to come because he’s bent over his brother’s knee, naked and hard…and fuck Sam didn’t think he could take thinking that way very much longer.  
  
“Yes, Dean. I'm your fuck toy.” Sam finally says and Dean’s hand circled lightly over the reddened skin of his ass.  
  
“That’s right.” Dean smacked again, once on each cheek in rapid succession. “I own you, Sam. I will play with you whenever I want to. I will tell you to come, or not to come.”  
  
“God, Dean, please.”  
  
Dean hit him again and Sam’s ass was practically glowing red. Sam's mouth kept moving, kept talking, though from the sound, Dean isn’t sure Sam is aware of what he’s saying. 'Please, mmm... oh God', follows 'christ, my fucking lord', which comes after 'please let me come, dear God, please'.  
  
Dean leaned back and he could see the Devil's Tail caressing the leaking swollen hardness of his brother’s prick. He watched fascinated and turned on as the Devils's Tail jerked his and Sam's cocks. Dean ran a hand over the redness of Sam's abused ass and eased Sam onto his knees on the floor beside the bed. Sam didn’t look up. There were trails of tears on his face, and his cock was dribbling a steady stream slicking the movements of the Devil's Tail. Dean stroked a finger over Sam’s face, ready to burst himself. “You are so damn beautiful, Sammy.”  
  
Dean’s kiss was tender and he paused to lick the tears away before he whispered in Sam’s ear. “I want to watch you come.” Sam shivered, and Dean's hand snaked down to remove the silver cock ring. He trailed his fingers across the Devil's Tail feeling it pulse and writhe around Sam's dick. He traced a line across Sam's hip and around to pinch his candy apple red ass. “Come for me now, Baby.”  
  
Sam’s eyes rolled closed and his body jerked and just like that he’s shooting streams of come across the room. Dean groaned, reaching for his cock, he squeezed the base hard trying to stave off his orgasm, because damn it, he needed to fuck Sam. He knows he won't last for long. Sam was still coming, with the Devil's Tail jerking him through his orgasm, when Dean pushed him down onto all fours. Dean grabbed the lube and fisted it onto his throbbing cock. His whole body was rigid like his dick as he positioned himself behind Sam, his hands on those red hot cherry cheeks.  
  
His hands gripped his brother’s narrow hips tightly knowing he would leave bruises as he slammed into him, forceful, powerful, ”Mine,” he growled through clenched teeth. He thought he saw Sam nod his ascent, but it doesn’t really matter. He was lost in the velvet crush of his brother's tight ass.  
  
Dean's hands slid up to Sam’s shoulders, yanking him backwards, marking his skin with bruises. “Say it.” Although Dean wasn’t exactly sure what he wanted him to say.  
  
Sam knew though, he pushed back against Dean, rose up to say the word over his shoulder. “Yours.”  
  
And fuck, Dean’s coming like a rocket. His hot spent filled his brother and oozed out around his softening cock as Dean pulled Sam back up onto his knees. He eased Sam back against his chest and licked a broad stripe up Sam's neck. “So fucking beautiful.” Dean whispered in his ear.  
  
Dean slipped out, moved off to get a washcloth and when he got back Sam was still kneeling there on the floor, come oozing out of him and painting the carpet all the way to the floor. Dean swiped the cool cloth over the sore spots, soothing and gentle, then moved to clean up his dick.  
  
Sam’s face was unreadable and it stopped him. Dean cupped his hand against Sam’s cheek, his thumb stroking over his lips. “Sammy, you okay?”  
  
Sam nodded a little stiffly, then his eyes moved, sliding up Dean to meet his eyes. What Dean saw there nearly had him hard all over again. “How did you know I wanted that?” Sam asked, his voice small.  
  
Dean gave him a gentle smile, “I didn’t. The Tail did.”  
  
Sam nodded and got to his feet. “I didn’t know until I felt your firm hand on me.” He blushed with the admission and Dean couldn’t help but close the gap between them and kiss him, his tongue delved deep into Sam’s hot wet mouth.  
  
“Its okay, Sammy. I’m going to take good care of you.” Dean whispered.  
  
Sam nodded, his breathing returning to normal. “I love you so much, Dean.”  
  
Sam’s kiss was tentative but Dean opened to his touch, let his kiss sweep through him. Sam sighed contentedly into Dean's mouth and stepped back. “I should shower.”  
  
“We both should.” Dean agreed with a wicked glint in his eye.

*-*-*-*

“Cas, I want you here now!” Dean called out to his angel.

Castiel appeared directly in front of him and Dean smiled hungrily at him. “Where were you , Angelcakes?”

“I was seeking a solution to our situation.” Castiel answered wondering why his vessel seemed to be short of breath and tingling.

The Devil's Tail was already busy disrobing the angel and exploring his taut slim body. Castiel felt his vessel's heart rate increase and his penis thickening and lengthening. Dean watched with a knowing smirk as all Castiel's clothes were removed.

“Dean, I find it hard to concentrate when my vessel is nude and being touched like this.” Castiel looked at Dean expectantly.

“I think you'd be able to concentrate better lying down by Sammy.” Dean was practically glowing and looked impossibly handsome backlit by the afternoon sun.

Dean led Cas to the bed and with the help of the Devil's Tail eased him down onto it. “There, are you comfy, Angelcakes?”

“Yes, Dean but this isn't improving my concentration.” Castiel's sapphire blue eyes latched onto Dean's jade green ones.

“Maybe this will help.” Dean climbed up between Castiel's legs and dipped his head. His lips closed around one nipple flicking the tip of his tongue over the hardening nub before tugging it between his teeth. Cas groaned and arched up off the bed all thoughts of his quest for a solution lost in a haze of passion. Sam was on his side watching then as the Devil's Tail caressed his tanned toned skin. Dean applied small wet kitten licks and sucking kisses over the skin of Castiel's chest and down his smooth taut stomach. He dipped his tongue into the angel's navel making him gasp and arch again. Dean moved lower sucking and nipping at the inside of Castiel's hipbone seeing the marks that Sam had left earlier. He licked down the angel's inner thigh and guided his legs farther apart. Dean chuckled as Cas moaned and writhed beneath him wantonly like a greedy cock whore.

The Devi's Tail was simultaneously stroking Sam's dick and probing the crease of his ass. Sam had leaned sideways and was tongue fucking Castiel with great enthusiasm. Castiel was lost to the erotic sensations of both Winchester's touching, licking, kissing, nipping and biting him.

Dean raised his head for a moment and watched Sam devouring Castiel's mouth and thought, damn that's hot. He had a wicked grin on his face as he lowered his head and sucked Castiel's balls into his mouth. He tugged at them gently and rolled them on his tongue.

Castiel had one hand on the back of Sam's neck as he returned the hot deep kiss from the younger Winchester. His other hand grasped the top of Dean's head as his hips bucked up thrusting into the wet heat of Dean's mouth. Dean hummed against the angel's balls for a moment before pulling off with an obscene slurping noise. Dean grasped the base of Castiel's leaking prick and steadied it as he licked up the underside making sure to pay special attention to the hot spot beneath the head. He swirled his tongue over the crown to capture every drop of pearly pre-come pumping his fist up and down the angel's rigid shaft. Castiel thrust up into his fist as Dean closed his lips in a tight seal around his cock and swallowed it all the way down to the base in one fluid motion.  
  
The head of Castiel's dick nudged the back of Dean’s throat, the muscles fluttering and squeezing around his length as Dean swallowed around his throbbing cock. Sam swallowed Castiel's desperate moans as Dean pinned the angel's slim hips to the bed to keep him still. Dean worked his mouth expertly on Castiel’s cock, sucking as hard as he could, pressing with the flat of his tongue at all of the angel's most sensitive spots.  
  
The Devil's Tail nudged Dean with the lube and Dean grabbed it never letting up his rhythm. He slicked the Tail with one hand and then slicked his own fingers. He kept working Castiel's cock as he slid those wet fingers between his spread legs and over the tight, clenched heat of his entrance. He rubbed small insistent circles over the pink bud, teasing him open as he deep throated his cock.  
  
Dean pushed inside, breaching him, past the tight ring of muscle, over the hot, ridged inner walls, and, angled his fingers, grazing deliberately over the small bundle of nerves there.  
  
Castiel's body convulsed as nearly electrical shocks of pleasure jolted through him. Sam released his mouth and listened as he keened sharply, sounding so deliciously helpless and exquisitely vulnerable as his prostate was repeatedly stroked. The Devil's Tail took that opportunity to enter Sam and mercilessly stimulate the bundle of nerves that shot sparks of pleasure through Sam's body and made him moan and shudder. Dean couldn't help but groan contentedly around his mouthful of cock and ground his painful erection down into the bed.  
  
“Dean.” Cas keened bucking his hips and arching up. Dean rubbed faster over the angel's sweet spot and sucked harder at his cock. Dean could feel Castiel's orgasm approaching. He pulled his mouth off and pumped him hard and fast with his tight fist.  
  
“Gonna come for me, Angelcakes?” he purred.

Castiel made a mewling sound deep in his throat that made Dean's dick twitch.  
  
“It’s okay, Cas. Come in my mouth. I want to taste you.”  
  
Castiel panted and keened as Dean took him back into his mouth while pressing a third finger inside his tight ass and rubbing hard.

The Devi's Tail was drilling into Sam nailing his prostate on every thrust and making Sam shudder and moan incoherently in pleasure. Sam looked over and watching Dean working Castiel's shaft and finger fucking him with abandon. Fuck, that's intense he thought before losing himself to the pounding pleasure of the Devil's Tail rocking and twisting and curling inside him.  
  
Castiel’s entire body contracted as the pressure peaked. His muscles knotted from the taut planes of his stomach, all the way down to his tightly curled toes. His hands dug into the sheets as his neck arched and spine bowed. His balls drew up, his dick pulsed, feeling like velvety silk over solid steel on Dean’s talented tongue as he shot his spunk in thick, hot, jets into Dean's waiting and eager mouth.

Sam cried out as he came, ropes of come painting the bed spread beneath him. The Devil's Tail continued to pound into his tight ass until he collapsed into his own sticky spent on the bed shivering and twitching with aftershocks.  
  
Dean worked Castiel through his orgasm until he was limp and spent. The angel collapsed back on the pillows enjoyed the sensations flowing through his satisfied vessel. Dean crawled up the bed like a tawny tiger keeping his jewel toned eyes locked on Castiel's flushed face. The angel surprised Dean by drawing up his legs, wrapping them around Deans back and pulling him down on top of him. Dean's burning jade eyes slid shut in ecstasy as his dick first nudged at Castiel’s entrance and then, with one steady thrust of his hips, pushed deep inside.  
  
He heard the angel's small pained mewl and kissed it away even as he worked his huge cock in and out of the tight heat, sliding a little easier since Castiel was so relaxed in his post-orgasmic haze.  
  
“You feel so damn good, Angelcakes. So fucking hot and perfect inside.”  
  
“Kiss me, Dean. Please?” Cas plead. His body was being rocked by Dean’s movements inside of him.  
  
Dean met his cobalt blue gaze and nodded. Moaning with abandon, their mouths locked together with rough passion as the pressure built and the tug and squeeze of the angel’s body sent Dean right up to the edge of the precipice.  
  
Dean pulled back to breathe as his orgasm hit him hard, white light beating behind his eyes, sparks of pleasure jolting his sweat slicked body. His hips rocked and twitched and slapped against the firm muscles of Castiel’s ass as he rode out his orgasm.  
  
Dean collapsed down onto Cas as he tried to catch his breath, before rolling them both over, their bodies still connected in the most intimate of ways, until Castiel was perched on top of him.  
  
Cas panted still feeling a little breathless as he settled himself on Dean's pelvis. Dean reached up and caressed the angel's cheek. “I'm discovering I have a deep love of Angel food cake. You really must stick around more, Cas so I can feed my cravings.”'  
  
“What if I have a craving, Dean, to get inside of you?” Cas asked as he wriggled a bit on Dean's cock.  
  
“You’re the bottom, Angelcakes. That means I get inside of you not the other way around.”  
  
“I'm on top of you now, Dean so doesn't that mean I should get inside of you?”

“Cas does have a point, Dean. He is on top of you right now.” Sam sided with the Angel just to push Dean's buttons.  
  
“Oh, I see, both my bottom bitches are trying to top me. Well, it's not gonna happen so you can put that thought right out of your heads.” Dean gave them both his fiercest dom look.  
  
“Well, that’s not fair, Dean. I think we should take turns.” Castiel looked completely serious and thoughtful while impaled on Dean's hardening cock.

“Yeah, Dean, Cas is right. We should take turns topping you.”  
  
“You both love when I fuck you. Spread your little asses out on my dick, fill you up and make you scream and purr.” Dean's eyes were glittering with lust as he started to thrust up into the perfect heat of Castiel's tight ass.  
  
“Uhhh. Dean,” Cas moaned, starting to rock his hips unconsciously.  
  
“I love the noises you make, Angelcakes.”  
  
Dean fisted the angel's hardened cock, feeling it swell and thicken even more as the heated words triggered something inside him, and started working him as he buried himself deep inside Castiel's body.

“ I see how it just drives you crazy how I can get so far up into you with my huge, thick cock, and fuck you so deep you’re practically choking on me. Love making you feel me, Cas. Touching you in the places that no one else has ever touched, making you feel things no one’s ever made you feel. Love fucking you, Angelcakes. Just gonna keep fucking you. Never gonna stop. Fuck you so hard…so long…make you ache and burn from me pounding your tight, hot ass.”  
  
Dean watched with lust blown eyes as Cas rose up and lowered himself back down taking every inch of Dean's dick deep inside him. “Gonna ride me, Angelcakes? Come on. Ride my cock. Show me how much you want it.”  
  
“Dean.” Castiel moaned, rolling his hips eagerly, rising up on Dean's shaft and pushing himself back down onto it.  
  
“You know you love it. You love having my thick cock buried in your little pink hole. Come on. Ride me harder, don't hold back on me.” Dean growled.  
  
Castiel moaned loudly, and worked himself more frantically on Dean’s dick. The Devil's Tail had stroked Sam back to hardness and was pumping into him as Sam watched Cas grind on Dean's cock. He gasped and shuddered as the Tail nailed his sweet spot over and over again. He briefly wondered if you could be fucked to death but the pleasure overwhelmed him and the thought was lost.

They all came together a few moments later and fell into a wet, hot pile of sticky limbs on the bed. Once again, Cas was in the middle of a Winchester brother sandwich and decided there really was no other place he would rather be.  
  



	3. Sin City

 

**The Devil's Tail Part 3 Sin City**

 

When Sam & Cas woke up, Dean was packing. “Sammy, pack your shit. We're getting the hell out of Dodge.”

Where are we gonna go, Dean?” Sam asked as he disentangled himself from Cas.

“We're going to Sin City, Baby!”

“Dean, I don't recognize that destination. Where is this place?” Cas asked his head tilted slightly.

“Angelcakes, it's Vegas as in 'Viva Las Vegas', as in 'what happens in Vegas', as in 'Sin City'!” Dean exclaimed.

“Dean, that is not an appropriate destination for an angel.”

“Angelcakes, where I'm gonna take you is so far from appropriate it's practically a different universe. Now, both of you hit the showers. We evac in 20.”

Sam and Cas hurried to follow his commands and Dean smiled smugly as the Devil's Tail fed deliciously illicit thoughts into his welcoming brain.

*-*-*-*-

Twelve hours later they arrived at the Blue Moon Resort which catered exclusively to gay male clients including such perks as a jacuzzi grotto, Roman baths and Cabana boys and was located close to the hottest gay clubs in Vegas.

“That's not the American flag. It has a rainbow on it.” Castiel observed at they got out of the Impala at the entryway.

Dean and Sam exchanged a look over the top of the Impala but didn't say anything. Dean made a mental note to take Cas to a Pride parade sometime. Dean and Sam grabbed their bags out of the back of the car as a valet walked up to take the Impala to the parking garage. Dean took in the black vest over bare toned chest and tailored pants that accentuated a nicely bulging package. If this was what the valet looked like he couldn't wait to see the Cabana boys!

They checked in and went up to their room aware that they were being eyed with open interest by other guests at the resort. Their room was a large suite with a California king pillow top bed. Dean smiled approvingly at the Jacuzzi bath and wondered how long Angelcakes could hold his breath. He grinned wickedly and told Sam and Cas that they should all grab a shower before heading out for the night. The Devil's Tail had been wrapped around Dean's waist and it was happy to be free again now that they were in the room away from curious eyes.

After the shower, Dean announced that they were all going shopping for new clothes. He wanted them all properly outfitted for this adventure and there was a shop just blocks away that should have everything they needed. Dean had a couple of platinum credit cards to break in and he was raring to go!

An hour later, they walked out of Extreme Leather ready for a hardcore night in Vegas. Dean walked out first in traditional leather pants. He was shirtless to show off his full leather harness that sported an attached cock ring. Sam followed close behind in modern cut leather pants that rode low on his hips so that the red band of this thong was visible peeking over the waistband. He was also wearing a leather half harness that drew attention to the exquisite musculature of his chest. Castiel came out last looking decidedly uncomfortable in his 'I Love My Dom' muscle shirt and skinny legged leather pants that molded to him like a second skin showing off his tight, pert ass. Sam and Cas were both getting used to the feel of the Steel Chastity Cock Cages that Dean had put on them at the store. The angel couldn't figure out why Dean had felt the need to cage his cock, after all, it couldn't go anywhere without him.

As they settled into the Impala Sam asked, “So where are we going first Dean?”

“We're going to Pole Riders, Sammy. Maybe you should go up on stage and show em how it's done!” Dean teased as the Devil's Tail slid across the seat and caressed Sam's sculpted abs.

“I've never seen a pole rider before, Dean.” Castiel commented from the back seat.

“Aw, Angelcakes. I have such sights to show you!” Dean chuckled as he imagined Castiel's reaction to the male dancers at the club.

When they arrived, Dean asked to speak to the manager. The mid forties man who looked a little like George Clooney came over to greet them. Dean, with the help of the tail, had won several thousand dollars at a casino stop on the way over to the club. He used some of the money to get them into VIP seating with one of the top three dancers at the club. They settled in front of stage where they would be up close and personal with their dancer. The owner sent him out to meet them. Dean, Sam and Cas were on their second Cock Sucking Cowboy with Spurs when a six foot tall adonis with shoulder length blond hair, blue green eyes and a killer smile strutted over to them in a black thong and black cowboy boots.

He walked right up to Dean and held out his hand, “Hi, ya' all. I'm Travis and I'll be your pole rider tonight.” He flashed a thousand watt grin and Dean returned it with one of his own.

“I'm Dean and this is Sam and Cas. Love the accent, Trav. What part of Texas are you from?” Dean asked.

“Tyler, Texas born and bred. I used to rodeo but this pays a lot better and I don't have to worry about any life threatening injuries. Is there anything in particular you'd like me to do tonight, Dean? You'll find I'm very flexible and pleasing the customer is my ultimate goal.” Travis drawled in his soft honeyed voice as he looked suggestively at Dean's package.

The Tail was wrapped around Dean's waist transmitting all sorts of filthy images to Dean but he resisted for the moment. “Make it rain, Trav, any way you want to.” He leaned forward and slipped a hundred dollar bill into Travis's thong and patted his package as he leaned back a knowing smirk on his handsome face.

Travis gasped and his eyes widened. Fuck, he was gonna give these boys one hell of a show. He went back to get his costume on and told the DJ to use Slow the Chemical Brother's extended mix. He put on the pull away assless chaps, leather snap vest and black cowboy hat. He looked in the mirror making sure he was suited up properly. He was used to middle aged, pot bellied bankers paying for the VIP show. These three guys were fucking nuclear hot and he was going to use all his best moves.

He took a deep breath at the curtain, heard his cue and pushed through stalking like a panther down the runway toward the the pole. Dean, Sam and Cas were watching with rapt attention as he jumped high on the pole doing three full rotations before stopping on the pole holding onto it with his legs. Travis leaned back, bowed his spine braced his hands, and made eye contact with Dean and winked. Travis released the pole doing a sort of back ward flip over and landing on his feet with his perfectly toned ass towards his audience. Dean wolf whistled appreciatively and threw some bills at Travis's boot clad feet. Travis executed a sensual undulating turn and ripped of his chaps throwing them off the stage. He dropped to his knees at the edge of the stage and did some dirty dancing for his attentive audience flinging his hat at Dean's feet. He rubbed his hands over every inch of tanned toned flesh as he undulated and writhed suggestively. He ripped off his vest and threw it to Castiel whose eyes were huge. Travis flipped over and humped the stage enthusiastically reaching behind his back to grab his boots and bow his body. He turned over braced his hands on the stage and pushed himself up pulled his legs back under and up until he was in a perfectly executed hand stand. From that position Travis angled his legs to grasp the pole then he pushed off the stage and up to grab the pole. It was a Cirque de Soliel move and it earned him a standing ovation and another rain of bills from Dean. Travis executed a few slick pole moves before dismounting and moving back up the stage to really tear loose and dance for his VIPs. Dean, Sam and Cas were all entranced. This guy could fucking move! He worked the pole a bit more till the music cue hit then he ran to the back of the runway. Travis knew this move would make it rain, sleet and snow. He took a deep breath, released and went for it. Dean wondered why he had gone to the back of the stage. Then Travis was flipping end over end doing three back flips a quick turn then two forward flips ending in the splits right in front of Dean as the song ended and one of the other dancers songs began.

Dean had given Sam and Cas a hand full of bills each earlier. He turned towards them now and said, “Make it rain boys!” The three of them showered Travis in green. He got on his knees so they had easy access to push bills into his thong.

When they got out to the car Cas said, “I like pole riders, Dean. They have amazing control over the musculature of their vessel and they are beautiful.”

“You'll get no argument from me, Angelcakes.” Dean smirked wondering what Cas would have to say about their next stop.

They drove up to a long black building that looked like it had been a warehouse in another life. The red neon sign said STACX. Dean had to chuckle as he thought about how Sam and Cas would react to what they found inside. The interior of the bar was huge and about 75% full of men is various leather fetish outfits. Cas and Sam were wearing fur lined locked leather collars to which Dean held the leashes. They stuck close to him a bit intimidated by the Dom Masters in the room. There was a huge sunken area in the middle of the bar. They could see several mens heads milling around in that area. In the very center of the sunken area was raised platform with a St. Andrews Cross on it. There was a spotlight highlighting the cross and drawing the patron's eyes to it. Dean led them to a table with a good view and ordered a round of Mind Erasers to calm Cas and Sam's nerves.

Cas looked down at the thirty or so men who were in the sunken area. They were all wearing collars and fetish shorts or thongs. “Dean why are those men standing down there?”

“Well, Angelcakes, they have all volunteered to be a part of tonight's entertainment. It should be starting any minute now.” Dean answered with a knowing smirk.

“Entertainment?” Cas looked at Dean expectantly for further information.

The crowd started to whistle, hoop and holler as three tall, tanned and ripped doms in executioner masks entered the area with the slaves. The slaves immediately dropped to their knees and touched their foreheads to the floor. The doms walked through them and stopped to look at each one. After a few moments, they chose one of the slaves and commanded him to rise. Dean thought he looked a bit like Antonio Banderas with his dark skin and jet black hair. The Dom Masters led him onto the platform and shackled him to the cross. The black thong left his taut cheeks bare to the audience and they roared their approval. Two of the Dom Masters stepped to the back of the platform as one stepped forward with a flogger in hand. The Dom stepped in close so he could run the flogger up the slaves spine. He said something to the slave and the slave answered. The Dom stepped back and with practiced flicks of his wrist landed six rapid fire blows all across the ass cheeks and upper thighs of the slave.

Dean looked over at Sam and Castiel's intent faces as they watched the scene unfold. The Devil's tail had slipped out and was caressing Castiel's tight ass in his painted on leather pants. Cas moaned a little and kept his eyes on the slave. Dean had slipped his hand down the back of Sam's pants and was pressing at his entrance. Sam pressed back against him breathing hard. His eyes glued to the platform. The first Dom stepped back and the second moved forward with a leather split crop. The slave tried not to flinch or make any noise under the rapid fire onslaught of the Dom's viscous attack.

“Dean, he's hurting him. Shouldn't we do something?” Cas looked genuinely concerned for the slaves welfare.

“He has a safe word, Angelcakes. If he wants the Dom to stop, all he has to do is say it.” Dean reassured the angel as the Devil's Tail distracted him by fondling his balls.

The second Dom moved back and the third moved forward. The whole crowd seemed to surge forward to watch him. The Dom unfurled his whip and made it snap by the slaves left ear. The slave recoiled and the Dom retaliated with a slash across his right ass cheek. Dean heard Sam and Cas both gasp at the sound of the whip biting into the slaves flesh. The Dom was relentless not giving the slave any time to recover between blows. The slave was sagging against his restraints now but he didn't say his safe word. The crowd was cheering and whistling and stomping their feet. The Dom landed a few dozen more blows then stepped back. The crowd went crazy as the Dom stepped forward pressing himself against the slaves ravaged back. He leaned in and whispered something to the slave who nodded vigorously. The Dom moved back grabbed the sides of the slaves thong and tore it off him. The crowd was in a frenzy now as the Dom shoved into the slave and rode him hard. Dean took in the total shock on Cas and Sam's faces as they watched the slave get fucked mercilessly by the huge Dom Master. When he finished the other two doms came forward and released the slave. The slave immediately turned, fell to his knees and cleaned up the Dom Master's cock. The crowd gave them all a standing ovation as they left the platform.

Dean looked to Cas and Sam and took in their lust blown eyes and panted breaths. He smirked as Cas looked at him and said, “ Dean, this cock cage is shrinking. It is uncomfortable and restraining.”

Dean leaned in close to the angel, “It didn't shrink, Angelcakes, you're getting hard. I think it's time to get you both back to the hotel for a little game of slap and tickle.”

*-*-*-*

Dean had Cas and Sam naked, hands against the wall, with their asses stuck out in invitation. He had stripped down to his harness with built in cock ring. He walked up behind Sam and stroked his hands up the inside of his thighs. Sam gasped at the touch and spread his legs wider. The Devi's Tail mimicked Dean's touch on Cas making him flinch and moan. Dean reached up between Sam's legs and closed his hand over Sam's sack. He rolled and fondled Sam's balls as he listened to him keen deep in his throat and fuck Dean loved that sound.

“Suck a cock whore. Listen to you, Sammy. I put my hand on you and you start moaning like a bitch in heat.” Dean purred the words against the nape of Sam's neck. Goosebumps raised under his breath and Sam keened again.

“I'm your cock whore, Dean.” Sam panted as Dean ran the fingers of his left hand down through the crease of Sam's ass. The Devil's Tail was still following Dean's lead and Cas was moaning and trying to thrust back against the tail. Dean grabbed a handful of the soft flesh of Sam's ass squeezing and kneading it, pulling him open. He pulled his right hand away from Sam's sack and commanded Sam to suck on his fingers and get them good and wet. Sam sucked them enthusiastically until they were dripping. Dean lowered his hand, twisted his wrist and pressed his middle finger into the center of the pink bud of Sam's opening. He felt a jolt of arousal and looked over to see Cas sucking on the Devil's Tail with wild abandon and fuck that was hot.

Dean growled. “Look, Sammy.”

Sam looked over and Dean simultaneously pressed his finger deep inside. Sam moaned and shuddered as he watched the angel suck the Devil's Tail. That was all kinds of dirty bad wrong and quite possibly the hottest thing he had ever seen.  
  
Sam gasped loudly and cried out as Dean rotated and fucked the finger into and out of him, squeezing at his balls at the same time. Dean hadn't touched Sam's cock yet but he's so hard and full that his prick is straining up against him dripping copious amounts of pre-come onto his taut stomach. Dean pressed in a second finger and fucked him faster and deeper as the Devil's Tail pulled out of Castiel's mouth with an obscene pop and moved back to plunge into his quivering hole. Dean released his grip on Sam's balls and squatted down to pick up the leather split crop that he had dropped there earlier. He rose up, pulled his fingers out and brought the crop down hard against the thickest part of the right cheek of Sam's ass. Sam groaned loudly and his cock twitched against his belly. Cas was watching as he ground back against the Devil's Tail that was pounding his prostate with unerring accuracy.  
  
“You love getting your ass whipped, don't you, Baby?” Dean purred.

Sam stuck his ass out even more as Dean smacked him with the crop again. Dean traced the marks that the crop had left with his fingers then he grabbed onto Sam's ass and squeezed the flesh, pulling his cheeks wide open.

Sam could feel Dean staring at his ass and panted, “Dean, please.” as he squirmed red faced under the intense scrutiny.  
  
“Oh, don’t be shy, Sammy.” Dean crooned. “I love to look at your pink little hole. I'm thinking of all the ways I’m gonna play with it and fuck it open.”  
  
Sam moaned as Dean traced small circles around the outer edge of his entrance with a thick finger. “Gonna whip you again, Baby, until your ass is cherry red and hot and throbbing. You just have to say one little word.” Dean was up against Sam's back now nipping at his pulse point as he teased his quivering hole with his thick finger.  
  
“Please.” Sam panted as he pressed back against Dean.

Dean stepped back and heard Cas cry out. He and Sam watched as the Devil's Tail thrust, twisted and vibrated inside the angel. Cas pushed back into the tail as he stroked his leaking cock and shuddered as he came across his hand and onto the wall.  
  
Dean released his tight grip on Sam’s cheeks pulled his hand back and brought the crop down on the round, fleshy part of Sam’s ass as hard as he could. Sam cried out, leaning his head against the wall, and Dean brought it down again and again. He smacked his ass until Sam started to anticipate the blows and tried to flinch out of the way when he thought that the next one was going to fall.  
  
Sam was breathing in little gasping gulps of air, and Dean paused for a moment letting Sam believe it was all over. Then he brought the crop down five more times in quick succession. Sam made a loud whimpering cry and Dean moved up behind him. He pressed their bodies together as he fisted Sam’s cock with one hand and with the other, pinched down hard on one of his erect nipples, rolling it between his thumb and index finger. He watched Sams eyes roll up in his head as he moaned and bucked his hips into Dean’s fist, fucking his hand. Dean jerked his hand even faster and harder and Sam keened desperately.  
  
“Gonna come, Sammy?”  
  
“Yes.”  
  
“Should I let you?”  
  
Dean stilled his hand and Sam whimpered.“Please. Dean.”  
  
“No. Not yet. Remember when you wanted to top me? You wanted to fuck me. If you want to come, then fuck my hand like it was my hot ass. Go ahead,” Dean coaxed, tightening his grip a little more. “Fuck my hand like you want to fuck my hole.”  
  
He can feel Sam resist the idea for a second. Then Sam gave in and snapped his hips forward, setting a rhythm as he fucked Dean’s hand.  
  
“That’s it. Fuck me, Sammy. Harder. Come on, Sammy. Give it to me. Fuck me.” Dean growled and Sam lost it choking off a rough yell as he came spurting hot and thick on the wall and all over Dean's fist.  
  
“Good boy,” Dean purred, pumping him through the aftershocks.

“Okay, boys, time to hit the shower then things are going to get really interesting.” Dean proclaimed with a wolfish grin.

*-*-*-*-

“I had some items delivered to our room. I think we're all going to enjoy them.” The Devil's Tail was twitching with anticipation.

Dean pulled a steel boned leather corset out of the box. “Come here, Cas. You are going to look so fucking hot all buckled in and barely able to breath. Now stand still.” Dean buckled Cas into the corset taking his 29 inch waist down to a 26. Cas could only take shallow panting breaths as his chest couldn't expand hardly at all in the corset.

“Sammy, get on the bed on your knees with your wrists down by your ankles. I've got something special for you too! A doggy style spreader! You're are going to look like a fucking porn star, Baby!” Dean smiled hugely.

Dean soon had the spreader bar between Sam's ankles and the restraints in place. He stepped back for a moment to look at Cas and Sam. Damn, he loved this town! You could have any perversion, fetish, or toy delivered right to your door!  
  
“Angelcakes, get on the bed. Lay back and pull your knees up and to the sides.”  
  
Still shaky and a bit dizzy from his orgasm, Cas climbed onto the edge of the bed and assumed the specified position. Dean's lust glazed eyes took in his two gorgeous subs and he thought fuck, they are hot! Dean climbed up the bed his eyes locked on the corset. He pushed Castiel's legs farther apart and settled himself between them.

“Dean, I can barely breath.” Cas gasped as the steel boned corset seemed to crush all his internal organs into one straining mass.

“Don't talk. Just concentrate on breathing.” Dean grabbed a pillow and propped up the angel's hips elevating his ass into a more accessible position.  
  
Dean dipped his head and dove in. He pointed his tongue, sticking it out as far as he could and plunged it into Castiel’s pink bud. He felt Cas stretch open around the rigid, wet muscle of his tongue. The angel gasped and arched up. The movement seemed to cut off even more of his limited airflow and he settled back onto the pillow trying to catch his breath.

The Devil's Tail had wrapped itself around Sam's shaft stroking him as it wound down between his balls and to his entrance. The Tail was teasing at the rim just pushing the very end of the tapered tip in and rotating a little as it continued to stroke and squeeze his cock and balls. With the spreader and restraints, Sam had very limited range of motion and he begged the tail to fuck him. The Tail pressed the arrowhead shaped head inside but didn't press in far enough to stimulate the bundle of nerves that would give Sam release.  
  
Dean curled and licked as deeply into Castiel's prefect tight heat as he could reach. His lips were pressed tightly to the Angel’s ass in an obscene kiss. He pulled back a little, removing his tongue and pulling Castiel’s ass apart again. Dean thickened his tongue and fucked the pink, saliva-slicked opening, quick and shallow, in and out of the outer ring of the angel's tight ass. Castiel keened softly trying to relax into the sensation and breath. Dean adjusted his grip. He pressed two fingers, one from each hand, into Cas and pulled him open so that he could lick in between. Castiel took harsh panting breaths as his body was jolted by the exquisite feel of Dean tonguing his ass. Dean worked his tongue and fingers deep inside of the angel's body. After a few minutes, Dean stopped, pulled his tongue free and licked long, wide, wet stripes up Castiel's thick shaft and over the weeping head collecting every drop of pre come. Dean pressed three thick fingers into the angel's spit slick hole and fucked him open more. Dean's eye's were locked on Castiel who was still panting and struggling for each breath inside the crush of the corset. Dean pushed a fourth finger inside and Cas gasped and pressed down on him.  
  
“You look so damn hot in that corset, Angelcakes. I’m going to fuck you so hard. Gonna ride your sweet ass until you beg me to come.”  
  
Dean shoved his fingers in deeper, curling them and stroking over Castiel’s prostate. Cas cried out his voice rough, raspy and breathless. His hips bucked up off the pillow. Dean looped his other arm under and around the angel’s hips, holding him still as he rubbed steadily against the sweet spot.  
  
“Please! Dean....” Cas gasped.  
  
“Sorry Angelcakes. I'm not gonna stop until you come.” Dean finger fucked him vigorously seeing the angel's cock leaking and twitching hearing the exquisite noises he was making. “Come for me, Angelcakes. Now.”  
  
Castiel’s breathing choked-off completely as his dick twitched and spasmed, unloading for the second time. All of his muscles went limp and Dean pulled his fingers out of his ass and cleaned up his cock. Cas made a strangled sound when he felt Dean's mouth on his oversensitive flesh. When Dean was finished, he leaned over pulled Sam's face to him and fed him Castiel's come. Cas watched and whimpered helplessly barely able to breath.

Dean pulled back from the heated kiss, “I hope you are both ready to get proper fucked. Cause the Tail and I are more than ready. Think I can get you to come for the third time, Angelcakes?”  
  
“No!” Cas rasped, not sure his vessel could survive being proper fucked in the corset.  
  
“Is that a challenge, Angelcakes?” Dean purred, his voice dangerously low.  
  
“ _NO!_ Please, can't breath.”

“On your hands and knees, Angelcakes. Don't make me ask twice.” Dean growled and Cas felt a bloom of heat in his groin and started to get hard again. What was it about that voice?!

Cas got into positon seeing spots in front of his eyes from lack of oxygen. His head was hanging down and he was struggling to expand his lungs just a bit more. Dean got in postion between his legs and his cock nudged at his stretched out entrance.  
  
“Are you ready for me, Angelcakes?” Dean didn't wait for an answer. He thrust deep into the hot velvet crush of Castiel's ass. He kept pushing deeper not stopping until his hips were flush against the angel's ass. Dean paused for a moment listening to Castiel's labored breathing. When Cas recovered enough to nod at him, Dean pulled back out then rocked his sensuous hips thrusting forward until he was balls-deep again. Cas keened and pushed back against him. Dean grabbed Castiel's hips and slammed into him harder making sure to nail his sweet spot. Cas trembled and cried out at the sensual assault on his senses. Dean drilled into him as hard as he could, skin slapping loudly against skin.

Cas began to wonder if Dean was going to fuck his vessel to death and exactly how would he explain that to the other angels? A sharp deep thrust brought him back to the moment.

Dean reached under Cas and pumped his hard leaking cock. “I want you to come with me, Angelcakes. I want to feel your ass clamp down on my cock.”

Cas was frantically pushing back on Dean's huge cock and pressing forward into his rough hand. His vision was starting to gray at the edges and he concentrated harder on his bodies frantic movements. When Cas came for the third time his velvet inner walls pressed like a vise on Dean's leaking cock. Dean thrust in a couple more times then came in pulsing jets deep inside the angel's fucked out ass. Castiel was barely conscious as Dean pulled out of him and stared down at the corseted angel's back.

Sam was writhing under the onslaught of the Devil's Tail. He looked over at Cas and Dean as his own orgasm ripped through him and left him shuddering and panting. Dean removed the corset, spreader bar and restraints from Cas and Sam. They were both practically boneless on the bed. He smacked their sore asses and commanded them to hit the showers. They looked for a moment like they might rebel but the fierce look Dean gave them erased those thoughts from their mind.

Later, they were all settled in the comfortable bed. “So what do you think of Vegas, Angelcakes?” Dean looked at Cas, his jade eyes sparkling.

“It's still not an appropriate destination for an angel but after tonight, I understand the sinful allure.” Cas answered solemnly his sapphire gaze holding Dean's.

When Dean broke the stare, he caught Sam looking dreamy and unfocused as he stared into the middle distance. Dean reached out, tucked a wayward strand of sable hair behind his ear and gently caressed his cheek, “What cha thinking about, Baby?” His deep honeyed voice was like a caress and Sam turned to look at him.

“I was thinking how much I'd like to watch you ride the pole at that club we went to tonight.”

“You were very good tonight, Sammy and every good slave deserves a reward. We'll make that our first stop tomorrow night.” Dean leaned in and kissed Sam licking deeply into his mouth and claiming him. He pulled away when Sam had gone boneless in his arms, “Goodnight, Sammy.”

He turned to the other side and pulled Cas in for a deep hard kiss until he was boneless as well, “Goodnight, Angelcakes.”

Dean scooted down on the bed between them and they curled into him. “Goodnight, Dean.” they chorused. He sighed contentedly as the Devil's Tail laid across his chest and they all slipped into a deep satiated dreamless sleep.

 


	4. The Michael Interlude

**The Devil's Tail** **Part 4**  
 **The Michael Interlude**

 

Dean was checking out pay per view while Cas and Sam were sleeping after a vigorous afternoon romp in the Jacuzzi. The Arch Angel Michael appeared between him and the television wearing the young John Winchester's meat suit. “Dean, you have strayed far off your true course. I'm here to refocus you on your task.”

Dean stood up. The Devil's Tail was transmitting a litany of delicious dirty thoughts that he was resisting. The Arch Angel was in his father. He couldn't submit to the Tail's dark desires. “I think I have my task well in hand. As long as I keep Sam sated he's not going to say yes to Lucifer and I'm sure as hell not going to say yes to you. So go back to Angel Band Camp or wherever you hang when you're not annoying the shit out of me. Go ahead, fly!” 

Michael shook his head. “I'm not one of your playthings, Dean. I don't obey your commands. We are going to figure out how to rid you of the tail and get you back on course.” 

The Tail twitched and exerted the full force of it's influence. Dean covered the space between himself and Michael. He wrapped one arm around Michael's waist and his other hand snaked behind the Arch Angel's neck. He leaned forward and latched onto Michael's lips. The angel gasped at this sudden sensual attack and Dean took full advantage of the opening. He captured Michael's tongue and sucked on it furiously as he ground his hips against him. The Devil's Tail had slipped into the front of Michael's jeans and was stroking his hard shaft as Dean thrust against him. 

There were snapshots in the Arch Angels mind of Lu above him body pressing into him. Passionate kisses and caresses that brought a heady mix of pleasure and pain as their bodies strained against each other. Stolen moments spent on earth exploring each others vessels. Discovering their limits and boundaries while experiencing a love so deep it burned him from within. Michael was overwhelmed for a moment. It had all gone so terribly wrong and now, here, at this moment balancing on the razor's edge, was the fate of the world he had sworn to protect. He should pull away. He should stop this insanity. The Devil's Tail knew how much Michael had missed the pleasures of the flesh. He hadn't had another lover since his father had forced him to banish Lu from Heaven. The Tail felt his heart opening up as his body started responded and his will weakened. The Tail had Dean deliver the coup de grace. It was such a simple thing really but The Tail knew it would break the Arch Angel completely.

Dean leaned back and stared into the intense deep blue eyes of the Arch Angel. Michael stared back into eyes that had turned ocean blue. Dean's hand left his neck and moved to cup his face gently, “Mica.” 

That one word but filled with such love and longing that Michael's heart melted and tears flowed from his eyes. “Lu.” Michael ran a finger tip down Dean's jaw then across his perfectly curved lips. A shudder ran through the Devil's Tail as it savored Michael's touch. Then Michael was kissing Dean with all the pent up passion of a lover denied the sweet bliss of his lover's embrace for far too long. 

 

When they finally pulled apart both of them were hard and aching for each other. Dean got an urgent prompt from the tail, “You know before we can share pleasure there must be pain. I have to punish you, Mica, for betraying me and casting me out. I have suffered such torment over these long ages while you stayed at our father's side. His good son. His perfect warrior never questioning the word of his father. You chose his regard over our love. If you truly desire me you will endure the pain to have me once again.”

“I will take the pain, Lu. I will endure so that I might experience once again the pleasures of the flesh. There has never been another. I have been and always shall be yours.” 

Since the Devil's Tail was piloting this ship it fed a suggestion to Dean and he relayed it to the Arch Angel. Michaels eyes widened in shock for moment then he recovered and reached up to touch a finger tip to Dean's forehead. 

 

They appeared on the raised stage at the STACX club. The spot light turned on like a light from heaven beaming down on the St. Andrew's Cross. “Strip!” Dean commanded in a deep aggressive growl. The Tail was twitching agitatedly behind his back anxious to get started.

 

Michael stripped off quickly flinging his clothes away carelessly. He stepped up to the St. Andrews Cross and meekly waited for Dean to shackle him in. Dean cinched the restraints tighter than was strictly necessary but it was what the Tail wanted so he complied. He went to the table at the corner of the stage and selected a few items then returned to the Arch Angel.

 

Dean put the black satin blind fold over Michael's eyes. He wanted the Arch Angel to concentrate solely on what he was feeling. Michael started to ask him to take it off but realized this was how it had to be so he remained silent. The Devil's Tail had Dean hug Michael from behind as it caressed his taut body for a moment. Then, as it had Dean pull back, the Tail tapped at a spot between Michael's shoulder blades. The Arch Angel gasped almost like he was in pain as his white iridescent wings sprung out and spread open. The Tail allowed itself to caress the sensual downy softness of the wings as Dean reached forward a look of wonder on his face and did the same. Michael gasped and writhed under their touch. His cock was aching hard against his stomach from the stimulation of having his wings fondled so lovingly. The Tail forced Dean to step back and take up the flogger.

Dean tickled the tails of the whip over Michael’s hard ass. He reached down between Michael's spread legs and rolled his balls across the palm of his hand. The touch was surprisingly gentle as he ran the flogger further up Michael's back. The Arch Angel sighed a little, turning his head to the side, his eyes hidden behind the blindfold. 

Dean released Michael's balls and took a step back. He flicked his wrist and the tails on the flogger spun in a circle then bit down on Michael's right ass cheek. Michael clenched his muscles and his glowing wings contracted closer to his body. He tilted his head towards Dean like he was listening for the sound of the whip sailing through the air again.  
  
The Arch Angel didn’t even flinch until the blows started coming harder and faster. Dean angled his wrist so one blow landed against Michael's balls. He cried out and tried to twist away instinctively from the pain. The restraints were so tight he couldn't get far so he hung his head and took a few deep breaths before settling back into position.  
  
When he started again, Dean aimed for that same spot, hitting it over and over again Michael writhed and moaned under the onslaught. Dean lashed out rapid fire a series of about seven blows causing Michael to yell out, “Please, stop for a moment.” But that’s not how the game was played, and the Arch Angel knew it. He was not surprised at all when Dean kept going not even pausing for a second. 

 

Michael was breathing hard, the air huffing out roughly through his parted lips. He sensed Dean was moving away from him. He wondered what the Tail had in mind for him next. The Arch Angel pulled on the bindings on his wrists, using the pressure to comfort and calm himself as he felt the flat tips of the leather split crop rub over his reddened balls. He groaned loudly, shaking his head a little.  
  
“Mica, I wish you could how beautiful you are. Glistening under the lights with your wings glowing like a beacon out of the darkness you locked me in for so long. I love you so much, my brother.” Dean purred against the Arch Angels neck and he traced along his spine with the crop giving him a moment to pull himself together. He had been a good sub and deserved this moment of quiet.  
  
Michael arched back, pushing into the touch, “Please, Lu, I need more.”  
  
The crop came down hard, three times right against his balls, and he cried out, his voice breaking a little. Dean ran the leather over his skin down between his legs and then up over his ass. Dean snapped his wrist back and brought down several hard blows onto both cheek's of Michael's muscular ass. He paused for a moment as Michael hung his head and panted in short breaths before starting another onslaught of leather against reddening tender flesh striking with increasing speed and force.  
  
Michael gritted his teeth, his eyes teared up behind the blind fold and he began to pull frantically at the bonds it has all become too much! “Lu!” Michael screamed the name his voice broken, begging his brother to stop.  
  
The last bite of the whip left deep red welts on his tortured flesh. Michael flinched at Dean’s gentle touch as he brushed his fingertips lightly over the Arch Angel's glorious wings. The Devi's Tail knew it was time for this particular punishment to end.

 

-*-*-*-*

Michael had transported them to a lush suite at the Wynn Encore in Vegas. The color scheme was white, gold and black. Dean had Michael laid out on the gold duvet his wrists in leather hand cuffs and the black satin blindfold securely in place. “I put the blindfold back on so you can't anticipate the hot wax. Ah, Mica, it has such a sensual feel. It slides onto the flesh with an intense heat and slickness that is like nothing else. I'm using Japanese Drip Candles. They are specially made for wax play. I've also got a bucket of ice to intensify the sensations. It's such sweet torture, Mica.” Dean leaned in and kissed Michael licking deep into his mouth loving the taste of him.  
  
Dean picked up the red candle and lit it. He watched the wax soften and pool at the tip like pre come. Dean straddled Michael's thighs sitting on them to hold him in place if he flinched away from the hot wax. Dean tipped the candle and a small blob of the red wax fell onto Michael's abs. Michael's whole body tensed and twitched at the feeling. He panted and writhed under Dean. The Devil's Tail urged Dean on and he started to move the candle letting the drips fill in the indentions around Michael's six pack abs. He followed the dips and curves as Michael moaned and writhed under him. When Dean had outlined his abs in red he put down the candle in a small lead bowl and reached into the ice bucket. He popped a couple of pieces of ice into his mouth and lowered his head. He let the icy water drip down his tongue and onto the wax cooling it as he traced the path of the wax across the Arch Angel's taut stomach. Michael tried to arch up into the exquisite sensation so Dean pushed down on his hips holding him in place. He got more ice cubes and continued to torture Michael with his talented tongue. 

 

Dean sat back and looked down at Michael, taking in his huge hard reddened cock. The Devil's Tail was tracing the red wax and pulsing with excitement. Dean popped a couple more ice cubes in his mouth and swallowed down the Arch Angel's cock all the way to the base. He kept a firm grip oh Michael's hips as he bobbed and sucked his cock. Dean's tongue pressed the melting ice cubes against the sensitive spot under the head of the Arch Angel's dick. Michael was shuddering and keening as the Devil's Tail peeled off the wax adding to the incredible rush of sensations that were overwhelming his brain.

 

“Lu, gonna come.” Michael cried out trying to warn his brother.

Dean just took him in deeper and hollowed his cheeks as he sucked even harder. Michael came with a strangled cry and flooded Dean's mouth with his release. Dean swallowed as much as he could momentarily stunned by the quantity and flavor. When he raised his head, there was come dripping down his chin. He crawled up Michael, took off the blind fold and commanded him to clean up his face. Michael leaned up and licked off all traces of his come. 

“Candy canes. You taste like candy canes.” Dean said a look of wonder on his face. The Devil's Tail twitched and a memory flooded through Dean. 

Mica and Lu had been sent to earth to experience Christmas. They were watching a huge parade in New York city. A man in a silly elf costume had come by and given them candy canes. Lu had loved the flavor and Mica had made sure he tasted like candy canes for Lu from that day forward. 

Den leaned in and kissed Michael deeply, lovingly savoring his taste and sharing it with him. 

 

*-*-*-*

  
When Dean and Michael appeared back at the Blue Moon Resort, Sam was shocked. “Dad, what are you doing here?!”

 

“This is Mica. I mean Michael, the Arch Angel.” Dean announced.

 

Michael greeted Sam and Castiel. Sam was staring at Dean wondering what the hell was going on. Why was Michael here and where had he and Dean been?

 

Dean put his arm around Michael's waist and Michael leaned against him as the Devil's Tail caressed him sensually. Dean's eyes locked on Sam's and Michael's eyes lock on Castiel's. A lot of silent communication took place and Sam felt a rush of heat to his groin. Dean looked down at the bulge in Sam's jeans and smirked wickedly. “Everybody strip, now!” Dean's deep growl of a voice had them all obeying instantly.

“Sam on your knees on the bed. Angelcakes here's your chance to show what you've learned. Prep him good then fuck him til he begs you to let him come!” 

“Yes, Sir!” Sam and Cas chorused in unison as they got in position. 

Dean laid back on the bed, “Want you to ride me Mica, like you used to. Put in the come thru penis plug on the night stand first then open yourself up for me.” 

Michael grabbed the come thru penis plug and lube and inserted it as Dean watched with hungry eyes. The Devil's Tail was stroking Dean's already hard cock and he was grateful for the cock ring he was wearing cause he didn't want to come too soon. Michael turned and braced himself against the dresser as he pressed a finger inside his tight pink bud and opened himself up for Dean. Dean was panting a little now and Michael pressed in a second finger and shoved back on it opening himself up wider. Then he heard Michael gasp and knew the heat from the ginger soaked penis plug was affecting him. Michael looked over his shoulder at Dean a question bright in his deep blue eyes.

“That's enough. Get over here and ride me, Mica!” The Devil's tail was vibrating with excitement as Michael straddled Dean's hips and stretched his pink rim over the head of Dean's huge leaking cock. He started to press down steadily and Dean leaned up, put his hands on Michael's shoulder's and pressed down hard. Michael cried out as he was impaled on Dean's dick. The Devil's Tail caressed and soothed him as he tried to catch his breath and adjust to the too full feeling. 

 

Castiel had worked Sam open with his tongue as Sam had turned his head to watch Dean and Michael. Seeing the Arch Angel submit to Dean was a bit overwhelming. Sam had a feeling that he and Cas had missed out on a lot of back ground story there. The feel of Castiel's wet velvety tongue working him open soon made coherent thought impossible and Sam moaned and pressed back into the sensation.

 

Castiel thrust his tongue deep into Sam vibrating against his inner walls then slipping in his index finger to stimulate the bundle of nerves that he knew would have Sam keening and begging to be fucked. Cas smiled when Sam cried out to him. He took a moment to look over at Michael preparing to lower himself on Dean's dick. He watched how Dean pressed him down hard onto him. Cas felt himself get impossibly harder and he breached Sam's entrance with a deep powerful thrust. Sam pressed back into him and encouraged Castiel to go deeper and harder.

Dean and Michael's eyes were locked on each other as Michael began to rise up and push down setting up a rhythm now as his body accepted the intrusion of Dean's thick shaft. The Devil's Tail stroked Michael's cock making the heat from the ginger dipped penis plug spread and deepen and burn. Michael was speeding up, swiveling his hips and almost dancing on Dean's dick. The Devil's Tail was pulsing and sending wave after wave of pleasure through Dean. He has his head back, neck beautifully arched, rocking his sensuous hips up as Michael lowered himself down. Dean was lost to the pleasure now. This was so intense and so perfect he didn't want it to end. 

Castiel pounded into Sam mercilessly nailing his sweet spot with each powerful thrust. Sam's fingers were digging into the covers and he was moaning deep in his throat. He could feel the heat pooling in his stomach as Cas sent shock waves of sensation through his body. 

 

Michael was lost in the ocean blue eyes of his lover; in the feeling of having a huge cock buried deep inside him. It had been too damn long since he had felt this. He deserved this surrender to the pleasures of the flesh. He sped up as he could feel his orgasm building, the sensation wrapping his spine and pooling in his belly. The Devil's Tail pressed into Michael as he was rising up again and his rhythm faltered. The sensation of the Tail and the huge cock inside him almost took his breath away. The Tail was moving in counter rhythm to Dean and Michael picked up the pace again.

Sam was begging Castiel to touch him, to let him come. Cas was liking this feeling of power over the younger Winchester. He reached under and started to stroke Sam firmly. Sam thrust into his fist and then pressed back onto his cock. He was very close to exploding. Castiel knew Sam was close so he drilled into him deeply while jerking him almost violently. Sam cried out as he came hot and hard over Castiel's hand and onto the cover. His ass clenched down around Cas and drew his release out of him as he collapsed against Sam's broad back and they sagged down onto the bed. 

Sam and Cas were watching as the Devil's Tail pulled out of Michael and started stroking his red swollen cock to completion. Michael was riding Dean with wanton abandon his hips shimmying and circling as he rose and fell over and over again. Michael came hard and the Devil's Tail aimed with the help of the come thru penis plug so Dean could swallow almost every drop of the candy cane flavored fluid. Sam and Cas looked at each other in disbelief. They hadn't know you could aim it like that! Dean came right after into the velvet crush of Michael's divine ass. Michael rode him through his orgasm then collapsed on top of him. 

 

They all snuggled up close and fell asleep in a warm tangle of limbs. Michael woke up with the voice of his father echoing in his head. He looked at Dean and the Devil's tail lying across his chest flicking slightly like the tail of a sleepy cat. The pain in is heart at the thought of leaving burned him but he could not refuse his father's command. He had always been the dutiful son. His father's perfect warrior. A warrior could not afford the weakness of love but he could dream of it and ache for it through all eternity. He pulled himself out of the crush of warm bodies. He paused and looked down at Dean's face. He looked younger and almost vulnerable while he was sleeping. He leaned down and pressed a gentle loving kiss to the sleeping hunter's lush lips. He allowed himself to lightly pet the Devil's Tail and heard what sounded like a soft purr from deep in Dean's throat. Michael smiled and his face was lit up with love and glowing with happiness for an all too brief moment then he was gone.   
  



	5. Retribution

The Devil's Tail Part 5

Retribution

 

Lucifer was standing in the rubble of a decimated town. There were tracks of tears down his ash stained cheeks. Mica had been on the earth and he had lain with Dean Winchester and the Tail. Lucifer couldn't banish the image from his fevered brain. Death appeared at Lucifer's side a ghastly smile on his gaunt face. Lucifer turned toward him, “I have some business to attend to. Continue with your mission and I will join up with you soon.”

Death nodded and disappeared from view. Lucifer stood among the smoking ruin of what had been a town and smiled. He would have his retribution. He would make all of them perform for him then he would have his fun with Dean Winchester.

“Get up whores!” Lucifer's deep booming command woke Dean, The Devil's Tail, Sam and Castiel from a deep sleep.

Dean looked around for Mica and was disappointed that the Arch Angel was no longer there. He, Sam and Cas climbed out of bed naked and lined up in front of Lucifer wondering what the hell was going on here.

Lucifer stepped forward and grabbed Dean's face in his large hands. He closed his eyes and let himself feel everything Dean and the Tail had felt with Michael. When the last image had faded he leaned forward and kissed Dean tasting Mica and candy canes. When Lucifer pulled back, a single tear rolled down his cheek and off his chin. “Fulfilling prophecies is an arduous task. I require a respite and entertainment before I continue. All of you will provide that for me.”

In a flash, Lucifer, Dean, Sam and Castiel appeared in a room. They could hear loud club music playing on the other side of the wall. Lucifer touched the Devil's Tail telegraphing his wishes then he took a seat to enjoy the show.

The Devil's Tail prepared Dean for what they were going to do in this room while a club full of people danced right outside the door to the thumpa thumpa of bass driven dance music. Dean understood that Lucifer was demanding some sort of recompense for him being with Mica. He hoped this would satisfy him.

Sam and Castiel were looking at Dean expectantly as he walked to a large trunk in the corner of the room and started pulling out items.

Dean walked purposefully over to his brother and stopped directly in front of his nude body, “Tonight, you do as you’re told, Sam. No questions. Do you understand me?” The command in Dean's voice was clear. His eyes were cold green glass reflecting nothing of Dean's thoughts or feelings.  
  
Sam’s eyes were stormy and dark as they locked onto Dean's but he didn't protest. He watched as Dean snapped a cock ring on him that had a chain leading up to a v and two nipple clamps. Dean teased one nipple with his tongue until it was standing erect enough for the clamp. Sam’s breath hitched as Dean attached it and moved to the other nipple.  
  
“Answer me, you filthy whore.” Dean spat at him for Lucifer's benefit.  
  
“Yes, Master. I understand.” Sam answered but his eyes were questioning.  
  
Dean adjusted the clamps and the chain until he was happy, then looked back up at his brother. “Good. Punishment will be swift and painful if you disappoint me. ”  
  
Dean put his hand on Sam's neck and pulled him close whispering to him softly so Lucifer didn't hear. Sam's eyes closed, he licked his lips and swallowed nervously. Dean looked at Castiel, grinned and tugged on the chain strung between Sam’s nipples making him gasp out loud his eyes flaring with a touch of defiance.

Dean turned toward Lucifer and The Devil's Tail began to caress Sam's broad back making it's way down to his muscular ass.  
  
Dean traced a line down Sam's jaw to his neck and lower. “Tell me what you need, you dirty whore.” Dean purred close to his ear.  
  
Sam stared at Lucifer and shook his head slightly. He wasn’t sure he could do this.

“Tell me, Slave.” Dean commanded. His hand closed on Sam's cock and squeezed hard.  
  
Sam’s eyes flicked to Lucifer, down to his cock, then back to Dean. “I need…” Sam closed his eyes as his voice trailed off.

Castiel reached out and put a comforting hand on Sam's shoulder urging him to continue before Lucifer punished them all.  
  
Dean leaned in close to Sam. “You want him to watch me fuck your tight ass, whore? Want him to see you with your cock all red and aching to come?”  
  
Sam’s eyes opened, their blue, green, gold lost to dark lust. “Yes. Please, Master.”  
  
Dean guided Sam to a padded bench with restraints for his arms and legs. He whispered softly to him, “It's okay, Baby. I gotcha.”

He pressed Sam down on the bench leaning over his back to growl in his ear as the Devil's Tail caressed his ass. “I'm gonna strap you in my greedy cock whore. Then I'm gonna fuck you until your eyes roll back in your head and you forget everything but your master's name. Dean's voice was a harsh growl that went straight to Sam's throbbing cock.  
  
Sam made a needy mewling sound and arched back against Dean.  
  
Dean straightened up, “Hey, Angelcakes, I could use an assist here.” Dean looked pointedly at Sam. Dean pointed at the legs of the bench. “Adjust these.” Dean indicated the shelves that pulled out for Sam's knees to rest on. He took the opportunity to stroke Sam's leaking cock as he waited for Castiel to obey his command.

Castiel leaned in and pulled out the shelves. Sam dutifully placed his knees on the shelves then Castiel swiveled them to pull Sam’s legs far apart, spreading him open.  
  
Dean got Sam into the proper position, strapped him down and petted him reassuringly when he felt him tremble. Having Lucifer here watching them was making them all ill at ease.  
  
“Hey Angelcakes, time to show me what you've learned. Give our eager cock slut a kiss and make me feel it.” Dean's jade eyes were locked with Castiel's sapphire blue conveying a deeper meaning to the angel who had marked him on the journey out of hell.  
  
Castiel leaned in and Sam stared up at him and nodded his understanding. Cas cupped Sam's face in his hands and kissed him slow. His tongue licked deep into Sam's mouth. Dean watched, a small secret smile curving his lips for a moment, then the mask of hard lines descended. He had the lube in his hand poised over Sam’s ass. Dean heard Sam moan and felt him relax against the bench. Sam started when the cold lube hit him. Dean stood behind his spread legs, drizzling lube over his upturned ass. The Devil's Tail continued to caress Sam soothingly as Dean worked two fingers into Sam opening him up. Castiel continued to kiss him deeply, distracting him from Lucifer's ominous presence. Dean, Sam and Cas were all achingly hard and ready to play.

Lucifer had to admit to himself that they were amazing together. He was thinking he might want to spend more time with them in such pursuits before the end of all things.  
  
Cas finally broke the kiss and looked over Sam's back to Dean, a question in his cobalt blue eyes. Dean held the stare for a moment then nodded.  
  
Sam’s eyes were fixated on Castiel's swollen red cock “Master, please, I want..” He husked and Dean felt it his plea course through him like lightening.  
  
“You want Angelcakes to fuck your hot mouth, my beautiful whore? Well, lucky for you, I want that too. Give our eager slurpy slut what he wants, Angelcakes. Make him take every inch.” Dean's eyes were blown black with lust and his voice was hoarse with restrained emotion.

Dean slicked himself up, his eyes on Castiel who was thrusting deeply into Sam's mouth. Dean lined himself up with Sam’s entrance and pushed in slow and steady. Sam moaned around a mouth full of angel cock and pressed back against Dean wanting him deeper. Dean gasped as the Devil's Tail unexpectedly thrust deep inside him. He paused for a moment and Sam whined in protest until he started to push deeper inside him.

Lucifer was finding this display extremely provocative. He was beginning to understand why Mica hadn't been able to reist Dean and the Devil's Tail.

Sam's tight inner walls were a crushing vise around Dean's engorged prick. He hadn't prepped him enough but the lube made up the difference and the bench was just the right height. Dean exhaled slowly as he was swallowed up in the velvet heat of Sam's ass.  
  
Sam’s head bent forward, cheeks hollowed out as he enthusiastically sucked Castiel's cock. Dean’s hands were anchored on his slim hips. His thumbs pressing against fading bruises from the last time Dean had taken him and owned him. Dean liked seeing those bruises knowing he had put them there.  
  
Cas made satisfied noises as Dean rocked into Sam, pulling nearly out, then thrusting back in. He went slow at first, hoping to hold his orgasm off. He had to admit to himself that it was a major fucking turn on having Sam totally restrained at he and Castiel's mercy while Lucifer watched them. Dean could admit to himself that he had a bit of a public sex kink and this was feeding it. He didn't even mind the tail teasing his prostate as he thrust into his brother. Sam was mewling, his body heaving. His hands pulled against the restraints as he hummed around Castiel's cock. Castiel tangled his fingers in Sam's long sable hair and threw his head back moaning in pleasure as he thrust in and out of the perfect wet heat of Sam's mouth.  
  
Dean unconsciously mirrored Castiel’s rhythm, pushing in as he pulled out. The Devil's Tail did the same and Dean had to bite down hard on his lip to keep from coming. He reached under Sam and tugged on the chain. Sam keened though the sound was nearly lost around the dick in his mouth. Dean changed his angle slightly and started to pound Sam's sweet spot with abandon. Sam thrust back against Dean clenching tight around him.  
  
Dean met Castiel's questioning stare and nodded then mouthed the countdown from five to one so they came at the same time. Castiel filled Sam's eager mouth and he gulped it down greedily, his eyes widening at the sweet familiar taste. Castiel smiled a secret smile down at him and winked conspiratorially. Dean squeezed Sam’s ass cheeks and pushed in, coming deep inside him and collapsing against him for a moment. He whispered, “You okay, Baby?” and waited for his answer before sliding out and back.  
  
His come oozed out of Sam, down his crack, down his swollen prick. Dean reached for it, smearing the sticky mess over the throbbing red shaft, pulling down. Sam’s whole body convulsed. His dick was leaking steadily. If not for the cock ring, he’d be spewing uncontrollably. Dean stroked him steadily then he released the cock ring. Sam’s mouth closed, opened and he was babbling words and non-words and shaking. Dean, Cas and Lucifer watched in fascination as Sam came spurting and crying out as a puddle formed on the floor beneath him.  
  
Castiel smiled and bent to kiss Sam again. He straightened up, then crossed to Dean, pulling him in for a kiss too. Dean tasted Lucky Charms cereal and when Cas pulled away he looked at him questioningly. Cas gave him a butter wouldn't melt in his mouth smile then the room disappeared.  
  
When Dean opened his eyes, he was on the bed in the black, gold and white themed room he had shared with Michael. Sam and Cas were sitting by the bed on two gold finished chairs. They were struggling but couldn't stand up. Lucifer's power was holding them in place. Dean couldn't move either and he felt profoundly uneasy being in such a vulnerable position. He looked down at the end of the bed to see Lucifer standing there with something that looked like a super size hat pin in his hand.

“You are a beautiful specimen of humanity, Dean Winchester. I can see why Mica couldn't reist your considerable charms. Ah, you've noticed the very special toy I brought to the party. You ever played with one of these before?” Lucifer held the silver device up in front of him so Dean could get a good look.

“It's a urethral sound. I haven't had the pleasure but I know what it is.” Dean met Lucifer's cold blue stare without flinching.

“I prefer to call it a vibrating penis probe. I always wanted to try it on Mica but he resisted the idea. You, on the other hand, don't have a choice.”  
  
Sam and Castiel were still struggling and Dean looked at them. His eyes told them to stop. They both calmed instantly and sat quietly watching as Lucifer pulled a small bottle of lube out of his pocket and climbed onto the bed.  
  
Lucifer sat next to him on the bed and opened the water-based lube. Out of his other pocket he produced a blindfold and instructed Dean to put it on. As Dean fitted the blindfold onto his face, Lucifer took hold of Dean’s dick firmly, and squeezed the lube into the slit in the head of his cock. Slicking a generous amount onto the sound as well, Lucifer set the tip of it at the opening of Dean’s urethra and started letting the slippery, heavy metal sound fall inside, its own heavy weight pulling it into Dean’s body.  
  
Dean hissed and fisted his hands into the gold duvet. Lucifer grabbed the lube again squeezed more onto the area where flesh met metal. The sound sunk deeper into Dean's dick. “Fuck!” Dean growled in a rough voice. He tried not to move. As long as Lucifer's attention was on him and not Sam, Dean would endure anything. He began to take deep calming breaths as Lucifer worked the sound in deeper. The sound was almost three inches inside now and the pain was starting to unnerve to him.

Lucifer added more lube when he felt resistance. He kept Dean's penis at the correct angle perpendicular to the body. He kept feeding the metal into Dean's cock. Dean continued his deep calming breaths and felt relief when Lucifer stopped pushing. “Honestly, I think you're going to like this, Dean.”

Lucifer smiled wickedly as he pressed the button and the sound started to vibrate at the same time he began to stroke Dean's cock to full hardness. Dean couldn't believe how the sound felt. He tried to fight the sensation but the vibration coupled with Lucifer's talented stroking fingers felt incredible. Dean moaned loudly and let the electric sexual current flow through his body.  
  
“Feels good, doesn't it, Dean?”  
  
“Oh, you have no idea…just keep going… I'm going to come.”  
  
Lucifer kept stroking Dean, using a finger to keep the sound deep inside. Dean's hips bucked up and he gasped, “I need to come, unhhh.”  
  
Lucifer moved his finger away continuing to stroke Dean's dick pushing the sound more and more out of his body. Dean gasped again as Lucifer grasped the end of the metal rod and pulled it the rest of the way out slowly as he continued to jerk him off.

As the end of the sound left his body, Dean yelled roughly as he spasmed, shooting spunk over his chest and Lucifer’s hand. Jerking him fast and hard, Lucifer worked him through it. Dean shivered with aftershocks on the bed. He pulled the blindfold off, looking at the mess covering him and at the wet-looking sound lying on the bed. He turned to see Sam and Castiel's stunned faces.  
  
“You have _**got**_ to try that,” Dean panted. “It was awesome!”  
  
Lucifer wiped his hand off and started to unzip his pants. Now, things were going to get really interesting. Dean Winchester was going to find out what pain really was. A blinding light whited out the room. Dean, Sam and Castiel covered their eyes. They heard Lucifer say 'Mica' then the light was gone as suddenly as it had appeared.

Dean was off the bed and Sam and Cas were out of their chairs all of them hugging each other tight. The Devil's Tail caressed each of them comfortingly.

“I thought he ...” Sam started to say. His lips close to Dean's ear.

“Dean, I...” Cas began at the same time.

“Shhh, it's all over. We're okay.” Dean soothed them both. They stayed huddled together for a few moments letting go of their fears. Dean knew he needed to bring his subs out of this. He needed to distract them and take care of them. It was his job. He pulled back enough that he could look at both their faces. He knew just the thing.

“Lucky Charms, Angelcakes?” Dean inquired with a smirk and a quirked brow.

“It's Sam's favorite cereal.” Cas answered somberly.

“What flavor would you give me?”

“Cherry Pie.”

“Is there any other kind?” Dean asked and chuckled.

They all looked at each other and busted up laughing. The tension was broken and they all felt that everything was going to be just fine.  
  



End file.
